196940-83-7

Upstream product

• 107-30-2 chloromethyl methyl ether 
• 217443-55-5 (2S,5R,Rs)-2-hydroxymethyl-5-methyl-2-(p-toluenesulfinylmethyl)tetrahydropyran 
• 196940-82-6 Methanesulfonic acid (3R,6S)-6-allyl-6-((R)-toluene-4-sulfinylmethyl)-tetrahydro-pyran-3-ylmethyl ester 
• 217443-52-2 Methanesulfonic acid (3R,6S)-6-propa-1,2-dienyl-6-((R)-toluene-4-sulfinylmethyl)-tetrahydro-pyran-3-ylmethyl ester 
• 217443-63-5 (2S,5R)-5-Methyl-2-propa-1,2-dienyl-2-((R)-toluene-4-sulfinylmethyl)-tetrahydro-pyran 
• 217443-54-4 (2S,5R,Rs)-5-methyl-2-((E)-1-propenyl)-2-(p-toluenesulfinylmethyl)tetrahydropyran 
• 217443-53-3 (2S,5R,Rs)-2-allyl-5-methyl-2-(p-toluenesulfinylmethyl)tetrahydropyran 

Downstream Products

• 71582-80-4 (-)-malyngolide 
• 217443-56-6 Acetic acid ((2S,5R)-2-methoxymethoxymethyl-5-methyl-tetrahydro-pyran-2-yl)-p-tolylsulfanyl-methyl ester 

Relevant academic research and scientific papers

Stereoselective synthesis of a 2,2,5-trisubstituted tetrahydropyran chiron via 1,3- and 1,6-asymmetric induction: A total synthesis of (-)- malyngolide

A new mode of synthesizing chiral 2,2,5-trisubstituted tetrahydropyran is described, in which two chiral centers are simultaneously introduced via facial and group selective nucleophilic acetal cleavage reaction of a bicyclic acetal 1, thereby accomplishing 1,3- and 1,6-asymmetric induction. It is revealed that acetal cleavage of the pro-R C-O bond and nucleophilic attack opposite the cleaved bond proceed preferentially. With TiCl4 and allyltrimetylsilane at -100 °C, the selectivity of acetal fission is 10:1 and that of nucleophilic attack is 12:1. This reaction is successfully applied to a total synthesis of marine antibiotics, (-)-malyngolide.